Y’all, this bourbon pineapple upside down cake is so incredibly good! The cake is extra moist, flavorful, and wonderfully spiced- topped with a killer and dreamy bourbon brown sugar glaze that soaks into the cake!

bourbon pineapple upside down cake on white dish

Spring is officially here you guys!!! How are we feeling exactly about it? Saying goodbye to winter is a little bittersweet for ya girl. I love the cozy vibes of that particular season and all of the warm recipes, however, I’m ready for the sun and all the goodness it brings. Andddd it’s getting brighter outside (the sun is out past 6pm, ha!)- we love to see it! The farmers markets are already slinging that beautiful seasonal bounty too.

Give me all the carrot cake, the strawberry, the lemon, and everything in between! Oh, and I’ll take a few of those Reese’s peanut butter eggs while I’m speaking. YASSS. The recipes that I have lined up for you are incredible, so pumped to share every single one. But let’s get into this bourbon pineapple upside down cake for a hot second. My friends, I’m a little biased but it is such a delight and a true showstopper!

bourbon pineapple upside down cake on white cake stand

The Best Bourbon Pineapple Upside Down Cake

When I tell you that this pineapple upside down cake is everything you could want in a sweet treat, I tell no lies. This cake is so easy to whip up, it’s loaded with flavor, baked in ONE single cake pan, and perfect for those small-scaled sweet cravings. Additionally, you’ll find most of the ingredients right in your pantry!

DISCLOSURE: This post is sponsored by Evan Williams Flavors who I’m so excited to partner with; and all thoughts expressed here are my own. As always, I am so grateful for brand partnerships like this!

You might be familiar with Evan Williams Bourbon, well, these folks also have launched their new flavors line! For example, you can find these flavors to include apple, peach, cherry, fire, and my personal favorite, honey. This is the flavored bourbon I’m using within this pineapple upside down cake and it is dang good. Furthermore, it combines the smoothness of their Straight Kentucky Bourbon with the sweetness of real, natural honey. To find Evan Williams Flavors nearest you in the US, check out their product locator.

bourbon pineapple upside down cake with bottle of bourbon on the side

Ingredients Needed For This Pineapple Upside Down Cake

(Note: the full ingredients list, including measurements, is provided in the recipe card directly below.)

  • For the bourbon brown sugar topping– this sauce thooo, so tasty + dreamy! You’ll need butter, brown sugar, vanilla bean paste or extract, bourbon, pineapple juice, and pineapple slices.
  • For the cake itself– you’ll need all purpose flour, white granulated sugar, baking soda, baking powder, salt, cinnamon, eggs, sour cream, vanilla extract, pineapple juice, and oil.

I love the flavors going on here within this bourbon pineapple upside down cake, y’all! The topping is super simple yet so rich, warm, and inviting. The butter adds richness, the brown sugar adds a touch of molasses flavor, the vanilla and pineapple adds more flavor and sweetness. And the bourbon rounds everything out with more depth and contrast. The whole beauty comes together nicely in a ten inch round cake pan!

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bourbon upside down cake slice on wooden plate with fork

Why You’ll Love This Cake

We all know that when it comes to cake, we like it moist without any dryness. Listen, this bourbon pineapple upside down cake did not come to play around! Thanks to sour cream and oil, a super moist cake is ensured. After testing this cake, I found oil to yield an even better outcome than butter. Also, once more, the combination of FLAVORS is so lovely here. We’ve got sweetness, richness, earthiness from the cinnamon, and more that all play against each other. The topping soaks into the cake and it is beyond delicious.

Can I Use An Alternate Flour?

Please know that this recipe has not been tested using any alternate kind of flours, so substitute at your own experiment. The only flour I would recommend as an alternate would be white whole wheat flour.

Can You Taste The Bourbon?

Nope! Not really because the small amount of alcohol is burned off within the sauce and is more of an extra flavor enhancer that adds some complexity within this pineapple upside down cake.

How Long Will This Cake Keep For?

If wrapped tightly in plastic wrap or kept in an airtight container, this cake will keep for up to three days when stored in the refrigerator. When storing in the freezer, this cake will keep for up to one month.

bourbon pineapple upside down cake on cake stand with cake slice on wood plate




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bourbon pineapple upside down cake on white dish

Bourbon Pineapple Upside Down Cake

  • Author: Quin Liburd
  • Prep Time: 5 minutes
  • Cook Time: 50 minutes
  • Total Time: 55 minutes
  • Yield: 6 1x
  • Category: Desserts & Sweets
  • Method: Baking
  • Cuisine: American


This bourbon pineapple upside down cake is so good! The cake is moist, flavorful, and wonderfully spiced- topped with a killer and dreamy bourbon brown sugar glaze that soaks into the cake!



Bourbon Brown Sugar Topping

  • 1/2 cup (1 stick) unsalted butter
  • 3/4 cup light brown sugar
  • 1 teaspoon vanilla bean paste, or vanilla extract
  • 20 ounce canned pineapple slices in pineapple juice, juice divided
  • 3 tablespoons Evan Williams Honey Bourbon

For The Cake

  • 1 1/2 cups all-purpose flour
  • 1/2 cup white granulated sugar
  • 2 teaspoons baking soda
  • 1 teaspoon baking powder
  • 1 teaspoon kosher salt
  • 1/2 teaspoon ground cinnamon
  • 2 large eggs
  • 1 cup vegetable oil, or canola oil
  • 8 ounces full-fat sour cream
  • 2 teaspoons vanilla extract
  • 1/4 cup pineapple juice, from reserved can of pineapple slices


  1. Preheat the oven to 350°F. Generously butter/spray a 10-inch round cake pan and set aside.
  2. For the bourbon brown sugar topping: In a small saucepan over medium heat, melt the butter. Once the butter has melted down, add in the brown sugar and whisk together with the butter. Add in the vanilla bean paste/extract and four tablespoons of the pineapple juice. Let the mixture come up to a nice simmer, about 2 minutes, while stirring every so often. 
  3. Turn off the heat and carefully pour in the bourbon and stir together to fully incorporate. The mixture will bubble vigorously for a quick second due to the alcohol. Then gently add in the pineapple slices in the same saucepan and use a spoon to coat each pineapple ring in the sauce. Let the saucepan hang so the mixture can sit together while you prepare the cake.
  4. For the cake: In a medium bowl, combine the flour, granulated sugar, baking soda, baking powder, salt, and cinnamon. Give everything a good whisk to fully combine. In another large bowl- combine the eggs, oil, sour cream, vanilla extract, and pineapple juice. Whisk the wet ingredients together to fully incorporate. Pour the dry ingredients into the wet ingredients bowl and use a rubber spatula to gently fold everything together until just combined. 
  5. To assemble cake: In the 10-inch round cake pan, take the saucepan and pour in a little of the sauce (just enough to fully coat the entire bottom of the pan). Then take each pineapple ring and place them all around the bottom of the pan. You may not be able to place each one in a single layer so feel free to overlap them or cut into pieces to fit all around. Then pour the remaining sauce evenly all over the tops of the pineapple rings. Carefully empty the cake batter on top and use an offset spatula/spoon to spread it evenly over the sauce/pineapple rings.
  6. Bake the cake for 45 minutes or until a toothpick inserted into the center of cake comes out clean. Allow the cake to sit in the pan for at least 10 minutes and then carefully invert the cake onto a large cake stand or plate as juices will run. Cut into slices and serve warm. Enjoy!


  1. You will need a 20 ounce can of pineapple slices in juice, about 10 pineapple rings. Alternatively, you can also use a fresh whole pineapple that is cut and cored.
  2. This cake will keep stored in an airtight container for up to three days when stored in the fridge and up to one month when stored in the freezer.
  3. Please read the blog post in its entirety for more tips + tricks.

Keywords: pineapple, cake, dessert, bourbon, sweets